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Synthesis of novel heterocyclic compounds based on dialdehyde cellulose: characterization, antimicrobial, antitumor activity, molecular dynamics simulation and target identification

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Abstract

In this study, new amino heterocyclic cellulose derivatives were prepared. Dialdehyde cellulose was functionalized by Schiff base reaction with (E)-2-(4-(dimethylamino) benzylidene)-4-oxo-4-phenylbutanehydrazide, (E)-2-((1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-4-phenylbutane hydrazide, and thiophene-2-carbohydrazide. The prepared derivatives were characterized and confirmed by Fourier-transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray, and Thermo gravimetric analysis. Additionally, antimicrobial activity of all derivatives was assessed as well as antitumor activity. Results revealed that, all derivatives have potential antimicrobial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Candida albicans, Cryptococcus neoformance, Aspergillus niger, A. fumigatus. Additionally, (E)-2-(4-(dimethylamino) benzylidene)-4-oxo-4-phenylbutanehydrazide and (E)-2-((1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-4-phenylbutanehydrazide cellulose compounds have good antitumor activities against Hep G2 and MCF7 cancerous cell lines without any effects on Wi38 normal cell line. Molecular dynamics study revealed that (E)-2-(4-(dimethylamino) benzylidene)-4-oxo-4-phenylbutanehydrazide and (E)-2-((1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-4-phenylbutanehydrazide cellulose derivatives have selectively target the ATP binding pocket residues. Identification of these ATP binding site residues and their crucial roles could provide the structure basis for understanding c-Kit kinase auto-inhibition

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Acknowledgments

The authors would like to acknowledge the support for this research from National Research Centre, Cairo, Egypt; and Faculty of Science, Al-Azhar University, Cairo, Egypt.

Funding

All expenses whether chemical analysis or molecular identification etc. were funded by ourselves and there is no funder or funding agency support us to finish this work.

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Authors and Affiliations

  1. Cellulose and Paper Department, National Research Centre, 33 El-Bohouth St. (Former El-Tahrir St.), P.O. 12622, Dokki, Giza, Egypt

    Mohamed Hasanin & Samir Kamel

  2. Botany and Microbiology Department, Faculty of Science, Al-Azhar University, Cairo, 11884, Egypt

    Amr H. Hashem

  3. Natural and Microbial Products Department, National Research Center, 33 El-Bohouth St. (Former El-Tahrir St.), P.O. 12622, Dokki, Giza, Egypt

    Ahmed A. El-Rashedy

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  1. Mohamed Hasanin
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  2. Amr H. Hashem
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  4. Samir Kamel
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MH research conceptualization, data curation, investigation, methodology, software, writing review and editing; AHH research conceptualization, data curation, investigation, methodology, software, writing review and editing; AAEl-R data curation, investigation, methodology, software, writing review and editing; SK research conceptualization, data curation, investigation, methodology, software, writing review and editing.

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Correspondence to Mohamed Hasanin or Amr H. Hashem.

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Hasanin, M., Hashem, A.H., El-Rashedy, A.A. et al. Synthesis of novel heterocyclic compounds based on dialdehyde cellulose: characterization, antimicrobial, antitumor activity, molecular dynamics simulation and target identification. Cellulose 28, 8355–8374 (2021). https://doi.org/10.1007/s10570-021-04063-7

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